Phosphated alcanol, its use as a hydrotrope and cleaning composition containing the compound

ABSTRACT

The present invention relates to the use of phosphated 2-propylheptanol or a phosphated 2-propylheptanol alkoxylate as a hydrotrope in aqueous alkaline solutions for a C 8 -C 18 -alcohol alkoxylate containing 1-20 ethyleneoxy units. It also relates to a phosphated 2-propylheptanol alkoxylate per se, and an alkaline cleaning composition comprising a C 8 -C 18 -alcohol alkoxylate containing 1-20 ethyleneoxy units and phosphated 2-propylheptanol and/or a phosphated 2-propylheptanol alkoxylate as a hydrotrope. The cleaning compositions may be used for industrial cleaning of hard surfaces, for example for vehicle cleaning or machine dishwashing.

This application is a continuation of application Ser. No. 11/632,380,filed Feb. 7, 2007, now U.S. Pat. No. 7,456,144 which is a NationalPhase Application of PCT Application No. PCT/EP2005/053267 filed Jul. 8,2005, which claims priority to European Patent Application No.04077043.0, filed Jul. 15, 2004 and U.S. Provisional Patent ApplicationSer. No. 60/608,167, filed Sep. 8, 2004.

The present invention relates to the use of phosphated 2-propylheptanolor a phosphated 2-propylheptanol alkoxylate as a hydrotrope in aqueousalkaline solutions for a C₈-C₁₈-alcohol alkoxylate containing 1-20ethyleneoxy units. It also relates to a phosphated 2-propylheptanolalkoxylate per se and an alkaline cleaning composition comprisingphosphated 2-propylheptanol and/or a phosphated 2-propylheptanolalkoxylate as a hydrotrope.

The ability of an aqueous solution to spread evenly over a surface, theso-called wetting ability, is important for many applications. Forexample, a composition for the cleaning of hard surfaces benefits from agood wetting of the surface. Good wetting is also desirable for laundryas well as for scouring and mercerizing processes. Nonionic surfactantsare known to be good wetting agents, and are often present incompositions for the cleaning of hard surfaces. Most often the hardsurface cleaning composition also contains alkaline components. Manynonionic surfactants are not soluble enough in solutions with a highamount of electrolytes, such as alkali and/or alkaline complexingagents, and therefore need the presence of a hydrotrope to improve thesolubility. A number of hydrotropes for nonionic surfactants have beendescribed in various publications. Examples of such hydrotropes areethanol, sodium xylene sulphonate, sodium cumene sulphonate, alkylglycosides, and phosphated alkoxylated alcohols.

In U.S. Pat. No. 5,145,597 alkaline cleaners useful in the cleaning ofmechanical equipment are described. These alkaline cleaners include aphosphate ester hydrotrope and a nonionic surfactant, but in the workingexample it is not specified which phosphate ester is used.

U.S. Pat. No. 4,493,782 describes a cleansing composition containing anethoxylated phosphate ester derived from an alcohol with between 8 and12 carbon atoms in the alkyl chain, which alcohol has been ethoxylatedwith 2-4 moles of ethylene oxide (EO). This phosphate ester is combinedwith another phosphate ester prepared from butanol+2 EO, where thelatter phosphate ester is added to stabilise the formulation.

U.S. Pat. NO. 4,137,190 discloses a detergent composition comprising anonionic surfactant and a synergistic hydrotrope mixture. In the workingexamples use is made of a combination of P₂O₅ phosphated phenol+6 EO andPPA phosphated butanol+1 EO or PPA phosphated isoamyl alcohol+4 EO.

U.S. Pat. No. 3,294,693 discloses hydrotropes for solubilisingpolyethylene oxide nonionic surfactants into builder solutions. Thehydrotropes are surface-active materials which contain upwards of 85%primary phosphate esters. These esters are formed by the reactionbetween PPA and an ethoxylated C₆ to C₁₀ alkyl phenol or an ethoxylatedC₁₀ to C₁₈ alcohol with 1-20 moles of EO. In all the working examplesphosphated octylphenol ethoxylates were used.

BE 632 444 relates to alkaline detergents comprising surface-activenonionic polyethylene oxide adducts, obtained by the addition ofethylene oxide to an alcohol, an alkylamine or an alkylphenol, and ahydrotrope which is a phosphate of an alkoxylated alkylphenol having6-10 carbon atoms in the alkyl group, or a phosphate of an alkoxylatedalcohol having 10-18 carbon atoms in the alkyl chain, and where thehydrotropic material contains 90% primary phosphate esters. In theworking examples several phosphated alkoxylated alkylphenols were usedas hydrotropes, as well as phosphated dodecylalcohol+15 EO andphosphated stearylalcohol+7.5 EO, to solubilise octylphenol+10 EO.

Orthophosphoric acid esters produced from alcohols that have beenethoxylated with up to 10, preferably 5, moles of ethylene oxide aredisclosed in EP-A-256427 as dispersants for pigments. 2-Propylheptanolis among the alcohols mentioned.

Alkali metal salts of mono- and diesters of orthophosphoric acid,produced from a number of alcohols, are disclosed in CH-A-481953 assurface-active agents used in a process for making a stable latex byemulsion polymerisation of vinylhalide monomers. Propylheptyl ismentioned as one possible alkyl substituent in these phosphates.

However, there is still a need for new efficient hydrotropes that aresuitable for certain compositions, since not all hydrotropes andnonionics are compatible for the achievement of clear, stable solutionsand an optimal performance in the application at hand. Especially, insome cases alkaline solutions containing a nonionic surfactant obtainedfrom an alkyl-branched alkoxylated alcohol and a hydrotrope willseparate upon dilution. An example of such alcohol alkoxylates are2-propylheptanol alkoxylates, where tests have shown that clear andhomogeneous, alkaline concentrates, containing alkylene oxide adducts of2-propylheptanol, and hexyl glucoside and/or an octyliminodipropionateas a hydrotrope, will become hazy or separate when they are diluted tomake ready-to-use solutions.

The aim of the present invention is to find a new hydrotrope that isefficient in making clear homogeneous concentrated alkaline compositionscontaining C₈-C₁₈-alcohol alkoxylates comprising 1-20 ethyleneoxy units,especially 2-propylheptanol alkoxylates, which compositions will remainhomogeneous upon dilution, and where the cleaning performance of thecompositions is good.

It has now surprisingly been found that phosphated 2-propylheptanol or aphosphated 2-propylheptanol alkoxylate where the alkoxylate on theaverage comprises 1-20, preferably 2-10, more preferably 2-6, even morepreferably 2-4, and most preferably 3, ethyleneoxy units and 0-3,preferably 0-2, propyleneoxy and/or butyleneoxy, preferablypropyleneoxy, units, is an efficient hydrotrope in an alkaline aqueoussolution for C₈-C₁₈, preferably C8-C₁₂, alcohol alkoxylates containing1-20, preferably 1-8, and most preferably 2-7 ethyleneoxy units and 0-3,preferably 0-2 propyleneoxy units, preferably for 2-propylheptanolalkoxylates according to the formula

where PO is a propyleneoxy group, EO is an ethyleneoxy group, a is anumber 0-3, and b is a number 1-8.

The invention further relates to aqueous cleaning solutions comprising

a) 0.2-20%, preferably 2-10%, by weight of a C₈-C₁₈, preferably C₈-C₁₂,alcohol alkoxylate containing 1-20, preferably 1-8, and most preferably2-7, ethyleneoxy units, preferably a 2-propylheptanol alkoxylate havingthe formula

where EO, PO, a, and b have the same meaning as above

b) 0.1-30, preferably 0.1-20, and most preferably 0.1-10% by weight ofphosphated 2-propylheptanol and/or a phosphated 2-propylheptanolalkoxylate, where the alkoxylate on average comprises 1-20, preferably2-10, more preferably 2-6, even more preferably 2-4, and most preferably3, ethyleneoxy units and 0-3, preferably 0-2, propyleneoxy units,preferably a phosphated alkoxylate according to the formula

where M is H, a monovalent metal ion or R₁R₂R₃R₄N⁺, where R₁, R₂, R₃,and R₄ are H, an alkyl group with 1-4 carbon atoms or —CH₂CH₂OH, and cis a number 1-20, preferably 2-10, more preferably 2-6, even morepreferably 2-4, and most preferably 3, and

c) 0.05-40, preferably 0.05-30, more preferably 0.05-20, and mostpreferably 0.05-15% by weight of an alkali hydroxide and/or alkalinecomplexing agents; which are homogeneous and stable, also upon dilution.The cleaning performance of these solutions is also very good.

Phosphated 2-propylheptanol or a phosphated 2-propylheptanol alkoxylatemay be obtained by different processes, the most common being thereaction of 2-propylheptanol or alkoxylated 2-propylheptanol withpolyphosphoric acid or phosphorous pentoxide (P₂O₅).

In the process using polyphosphoric acid the resulting product mixturewill predominantly contain the monoalkylphosphate ester of2-propylheptanol or of alkoxylated 2-propylheptanol and only a smallamount (<10%) of the dialkylphosphate ester. Always rather large amountsof inorganic phosphate residues from the polyphosphoric acid, such asorthophosphoric acid, will be present.

When P₂O₅ is used as the phosphatising reagent and the molar ratiobetween P₂O₅ and alcohol or alkoxylated alcohol is 1:3, the productmixture will contain about equal amounts of monoalkylphosphate ester anddialkylphosphate ester, and only smaller amounts of inorganic phosphateresidues. A larger amount of alcohol or alkoxylated alcohol will yieldmore diester, and a smaller amount will yield more monoester. It will beknown to a person skilled in the art how to synthesise phosphate esterswith certain amounts of mono- and dialkyl phosphate esters. For ageneral description of phosphate esters see, e.g., Anionic SurfactantsVol. 7, Part II, pages 504-511 in Surfactant Science Series, edited byWarner M. Linfield, Marcel Dekker Inc., New York and Basle 1976. Thealcohol alkoxylates to be phosphated may be either of the standard typeproduced by using an alkaline catalyst such as KOH, or of the narrowrange type produced by using a narrow range catalyst, such as an acidcatalyst, Ca(OH)₂ or hydrotalcite.

Normally the reaction mixture resulting from either of the procedureswill be neutralised by an organic or inorganic base before use. The basemay be, e.g., an alkali hydroxide, such as sodium hydroxide or potassiumhydroxide; ammonia, an alkanolamine, such as monoethanolamine,triethanolamine or methyldiethanolamine; or an alkylamine such astriethylamine.

The monoalkylphosphate ester of 2-propylheptanol or of ethoxylated2-propylheptanol has the formula

where M is H, a monovalent metal ion or R₁R₂R₃R₄N⁺, where R₁, R₂, R₃,and R₄ are H, an alkyl group with 1-4 carbon atoms or —CH₂CH₂OH, and cis a number 0-20, preferably 2-10, more preferably 2-6, even morepreferably 2-4, and most preferably 3. The product mixture resultingfrom the reaction of 2-propylheptanol or of ethoxylated 2-propylheptanolwith polyphosphoric acid may also contain smaller amounts of productscontaining more than one phosphate unit according to the formula

where n is 1-3 and M and c have the same meaning as above.

For ethoxylates containing smaller amounts of ethyleneoxy units, also acertain amount of unethoxylated product will remain due to thedistribution of ethyleneoxy units. This unethoxylated product will alsobe phosphatised during the reaction with the phosphatising agent, andthus the phosphate ester of 2-propylheptanol will also be present in thereaction mixture resulting from these above-mentioned ethoxylates.

The dialkylphosphate ester of 2-propylheptanol has the formula

where M and c have the same meaning as above. The product mixtureresulting from the reaction of 2-propylheptanol or ethoxylated2-propylheptanol with P₂O₅ may also contain a dialkyl diphosphate esteraccording to the formula

where M and c have the same meaning as above. This type of diester maybe hydrolysed to yield 2 moles of monoester.

2-Propylheptanol is normally made by a process resulting in smallamounts of by-products such as 4-methyl-2-propylhexanol and5-methyl-2-propylhexanol. These products or their ethoxylates will alsobe phosphated during the process, and the phosphated species will becomprised in the resulting product mixture.

The reaction mixtures obtained by the phosphatising procedures arenormally used as such without any purification procedure, but both themixtures and the purified phosphate esters function as hydrotropes. Toact as a good hydrotrope, the mixture should predominantly contain themonoalkyl phosphate esters, since these are better hydrotropes than thedialkyl phosphate esters. Preferably more than 60, more preferably morethan 70, and most preferably more than 80% by weight of the mixtureshould be monoalkyl phosphate esters.

The phosphated 2-propylheptanol or phosphated 2-propylheptanolalkoxylates where the alkoxylate on average comprises 1-20, preferably2-10, more preferably 2-6, even more preferably 2-4, and most preferably3, ethyleneoxy units and 0-3, preferably 0-2, propyleneoxy and/orbutyleneoxy, preferably propyleneoxy, units described above and aprocess for their production are already partly disclosed in the earliermentioned publications EP-A-256427 and CH-A-481953 for use asdispersants for pigments and as additives in an emulsion polymerisationprocess, respectively. However, the phosphated 2-propylheptanolalkoxylate where the alkoxylate comprises 2-4, preferably 3, ethyleneoxyunits on average is especially efficient as a hydrotrope compared to theother phosphated alkoxylates of 2-propylheptanol (see Table 1 in theExamples). Therefore, the invention also relates to the phosphated2-propylheptanol alkoxylate where the alkoxylate on average comprises2-4, preferably 3, ethyleneoxy units per se and a process for itsproduction.

The C₈-C₁₈-alcohol alkoxylates may, in addition to the 1-20 ethyleneoxyunits, also contain 1-3 alkyleneoxy units with 3-4 carbon atoms. Theethyleneoxy units and the propyleneoxy and/or butyleneoxy units may beadded randomly or in blocks. The blocks may be added to the alcohol inany order. The alkoxylates may also contain an alkyl group with 1-4carbon atoms in the end position. Preferably, the alkoxylates contain2-7 ethyleneoxy units and 0-2 propyleneoxy and/or butyleneoxy units.

A suitable alkoxylate to be used in the cleaning composition for thecleaning of hard surfaces has the formula

where PO is a propyleneoxy group, EO is an ethyleneoxy group, a is anumber 0-3, preferably 0-2, and b is a number 1-8, preferably 2-7, andmost preferably 3-6. When the 2-propylheptanol contains the by-productsmentioned above, these will also be alkoxylated and comprised in theresulting product mixture. The cleaning concentrates obtained by usingthe phosphated 2-propylheptanol alkoxylates as hydrotropes for the2-propylheptanol alkoxylates are clear and stable, also upon dilution,and cleaning compositions with these components exhibit a good cleaningperformance.

When the cleaning composition is to be used for textile applications,such as for laundry, then the alkoxylate a) should preferably comprisean amount of ethyleneoxy units in the upper part of the range 1-20, forexample 7-15 moles of EO per mole of C₈-C₁₈-alcohol.

The alkali hydroxide in the composition preferably is sodium orpotassium hydroxide. The alkaline complexing agent may be inorganic aswell as organic. Typical examples of inorganic complexing agents used inthe alkaline composition are alkali salts of silicates and phosphatessuch as sodium silicate, sodium metasilicate, sodium tripolyphosphate,sodium orthophosphate, sodium pyrophosphate, and the correspondingpotassium salts. Typical examples of organic complexing agents arealkaline aminopolyphosphonates, organic phosphates, polycarboxylates,such as citrates; aminocarboxylates, such as sodium nitrilotriacetate(Na₃NTA), sodium ethylenediaminetetraacetate (EDTA), sodiumdiethylenetriaminepentaacetate, sodium1,3-propylenediamine-tetraacetate, and sodiumhydroxyethylethylenediaminetriacetate. The amount of alkali present inthe composition depends on the application and on whether thecomposition is a concentrate or a ready-to-use solution. Someapplications use highly alkaline solutions; for example for scouring,the alkali concentration is c. 4-6% by weight when using NaOH, and formercerization, a ca. 20-26% by weight caustic soda solution is used. Aconcentrate composition for vehicle cleaning normally contains 6% to 15%by weight alkali and/or alkaline complexing agents, and the ready-to-usesolution normally contains 0.2 to 5% by weight. For laundry, the amountof alkali and/or alkaline complexing agents is lower and normallyamounts to 3 to 10% by weight in the concentrate and 0.1 to 1% by weightin the ready-to-use solution.

The concentrated compositions of the present invention are clear andstable. The clarity interval is suitably between 0-40° C., preferablybetween 0-50° C., and most preferably between 0-60° C. This may beadapted by changing the ratio of hydrotrope to nonionic surfactant. Theconcentrate normally contains 50-95% by weight of water, suitably 70-90%by weight.

To obtain a ready-to-use solution the concentrates are diluted withwater up to 1:40. The diluted solutions are also clear and stable, butin some cases they may turn a little bit hazy although they are stillstable and do not separate. The ready-to-use solutions exhibit goodcleaning properties. A typical concentrate formulation for vehiclecleaning contains 3-5% by weight of a), 3-5% by weight of b), and 5-10%by weight of c), and a ready-to-use formulation would normally contain0.2-1% by weight of a), 0.2-1% by weight of b), and 0.5-1% by weight ofc).

The present invention is further illustrated by the following Examples.

EXAMPLE 1

Formulations were made containing:

5% by weight of a nonionic surfactant

10% by weight of Na₃NTA (sodium nitrilotriacetate)

X% by weight of hydrotrope

Balance water

The hydrotrope was added in such an amount that the solution exhibitedthe clarity interval stated in Table 2. All percentages are by weight.

TABLE 1 IV (Com- Compound I II III parison) V VI VII Phosphated 4.4%5.9% 2-PH¹ Phosphated 3.2% 4.2% 2-PH + 3EO² Phosphated 5.4% 6.1% 2-PH +5EO³ Coco fatty 3% amine + 17EO quaternised with CH₃Cl C₉-C₁₁-   5%   5%  5% 5% alcohol + 4EO 2-PH + 5EO   5%   5%   5% ¹2-PH = 2-propylheptanol²2-PH + 3EO = 2-propylheptanol ethoxylated with 3 moles of ethyleneoxide ³2-PH + 5EO = 2-propylheptanol ethoxylated with 5 moles ofethylene oxide

To evaluate the cleaning efficiency of the formulations in Table 1 thefollowing cleaning test was used: White painted plates were smeared withan oil-soot mixture obtained from diesel engines. 25 ml of the testsolutions, in this case the formulations in Table 1 diluted 1:20, werepoured onto the top of the oil-smeared plates and left there for oneminute. The plates were then rinsed off with a rich flow of water. Allsolutions and the water were kept at a temperature of about 15-20° C.All reference solutions were placed on the same plate as the testsolutions. The cleaning ability was measured with a Minolta Chroma MeterCR-200 reflectometer, and the result is presented as the % soil removal.The results are collected in Table 2.

TABLE 2 Appearance Soil removal at Formulation Clarity interval afterdilution 1:20 dilution No (° C.) 1:20 (%) I 0-50 Hazy but stable 77.5 II0-46 Clear 83.0 III 0-45 Clear 81.5 IV 0-80 Clear 69.5 (comparison) V0-75 Hazy but stable 71.5 VI 0-60 Clear 74.0 VII 0-60 Clear 73.5 IV 0-80Clear 63.0 (comparison)

The formulations containing phosphated 2-propylheptanol or phosphated2-propylheptanol ethoxylates as a hydrotrope exhibited a better cleaningperformance than the comparison formulation containing coco fattyamine+17 EO quaternised with CH₃Cl. There are two values for thecomparison compound, since the cleaning efficiency was tested on twoseparate plates; one with I, II, III, and IV and the other with V, VI,VII, and IV.

EXAMPLE 2

This example relates to a comparison between phosphated2-propylheptanol+5 EO and phosphated hexanol+5 EO as hydrotropes for2-propylheptanol+5 EO.

TABLE 3 Formulation B Compound Formulation A (Comparison) Phosphated2-PH + 5EO 3.5% Phosphated 4.9% hexanol + 5EO 2-PH + 5EO 5.0% 5.0%Sodium metasilicate 4.0% 4.0% Tetrapotassium 6.0% 6.0% pyrophosphateWater 81.5% 80.1%

TABLE 4 Soil removal Clarity Appearance Appearance Appearance Appearanceat 1:20 interval after dilution after dilution after dilution afterdilution dilution Formulation (° C.) 1:1 1:5 1:10 1:20 (%) A 0-60 ClearClear Hazy Hazy 68.5 but stable but stable B 0-60 Separated SeparatedSeparated Separated 70.5 (comp.) IV 0-80 Clear Clear Clear Clear 62.8(comp.)

A smaller amount of phosphated 2-propylheptanol+5EO, as compared tophosphated hexanol+5EO, was required to obtain a clarity interval of0-60° C.

The formulations with phosphated 2-propylheptanol+5 EO as a hydrotropeexhibited about the same cleaning efficiency as the formulations withphosphated hexanol+5 EO, but the former were much more stable whendiluted than the latter.

EXAMPLE 3

This example compares a number of phosphated ethoxylated alcohols withphosphated 2-propylheptanol+5 EO as a hydrotrope for 2-propylheptanol+5EO.

TABLE 5 4 2 3 (Compari- Compound 1 (Comparison) (Comparison) son) 2-PH +5EO 5.0% 5.0% 5.0% 5.0% Phosphated 2- 3.5% PH + 5EO Phosphated 3.0%C₉-C₁₁-alcohol + 5.5EO Phosphated 3.4% C₉-C₁₁-alcohol + 4EO Phosphated2- 3.0% ethylhexanol + 4EO Sodium 4.0 4.0 4.0 4.0 metasilicate Tetra-6.0 6.0 6.0 6.0 potassium pyrophosphate Water 81.5 82.0 79.0 82.0

TABLE 6 Soil Appearance Appearance Appearance Appearance removal Clarityafter dilution after dilution after dilution after dilution at 1:20interval 1:5 after 1 1:20 after 1 1:5 after 1 1:20 after 1 dilutionFormulation (° C.) day day week week (%) 1 0-70 Clear Clear Clear Hazybut 60.0 stable 2 (Comp.) 0-53 Clear Clear Clear Clear 26.0 3 (Comp.)0-60 Clear Clear Clear Clear 44.0 4 (Comp.) 0-50 Hazy Hazy Cloudy Hazy54.0

The formulation according to the invention exhibited the best cleaningperformance of all the investigated formulations, in combination with agood stability upon dilution.

EXAMPLE 4

Table 7 displays formulations where the same amount of hydrotrope wasadded to all formulations. The cleaning efficiency of the differentformulations is shown in Table 8.

TABLE 7 Compound 5 6 7 (Comp.) 8 (Comp.) 9 (Comp). 2-PH + 5 EO 5.0% 5.0%5.0% 5.0% 5.0% Phosphated 2- 3.7% PH + 3 EO Phosphated 2- 3.7% PH + 5 EOPhosphated 3.7% C₉-C₁₁-alcohol + 5.5 EO Phosphated 3.7% C₉-C₁₁-alcohol +4 EO Phosphated 2- 3.7% ethylhexanol + 4 EO Sodium 4.0 4.0 4.0 4.0 4.0metasilicate Tetra- 6.0 6.0 6.0 6.0 6.0 potassium pyrophosphate Water81.3 81.3 81.3 81.3 81.3

TABLE 8 Soil Soil Appearance Appearance removal removal Clarity afterdilution after dilution at 1:30 at 1:40 interval 1:5 after 4 1:20 after4 dilution dilution Formulation (° C.) days days (%) (%) 5 >60 ClearClear 50.0 40.0 6 50 Clear Clear 61.0 47.0 7 (Comp.) 51 Clear Clear 16.013.0 8 (Comp.) >60 Clear Clear 27.0 20.0 9 (Comp.) >60 Hazy Hazy 36.021.0

The formulations according to the invention are more efficient than thecomparison formulations.

EXAMPLE 5

In this example phosphated 2-propylheptanol+5 EO was added as ahydrotrope to a number of nonionic surfactants, and the formulationswere tested for their cleaning efficiency.

TABLE 9 Compound 10 11 12 13 Phosphated 5.5 2.8 2.5 2.3 2-PH + 5EOC₉-C₁₁-alcohol + 5.0 4EO 2-ethyl- 5.0 hexanol + 4EO C₉-C₁₁- 5.0alcohol + 5.5EO 2-ethylhexanol + 5.0 2PO + 4EO Sodium 4.0 4.0 4.0 4.0metasilicate Tetrapotassium 6.0 6.0 6.0 6.0 pyrophosphate Water 79.582.2 82.5 82.7

TABLE 10 Appearance Soil after dilution removal at Clarity interval 1:20after 1 1:20 dilution Formulation (° C.) month (%) 10 0-45 Clear 71.0 110-50 Clear 41.0 12 0-49 Clear 65.0 13 0-50 Slightly hazy 76.0 but stable

The results show that phosphated 2-propylheptanol+5 EO also works as ahydrotrope for other nonionics than 2-propylheptanol alkoxylates, andthat the cleaning efficiency for these formulations in general is good.

EXAMPLE 6

In this example the wetting ability of a composition according to theinvention was measured by the modified Drave's test.

TABLE 11 Compound C Phosphated 2-PH + 5EO   6% C₉-C₁₁-alcohol + 4EO 5.0%Sodium nitrilotriacetate 10.0% 

In the modified Drave's test, the sinking time in s is measured for aspecified cotton yarn in approximately 0.1% surfactant solution. Theformulation in the Table above was diluted with distilled water to 0.1%by weight with respect to the C₉-C₁₁-alcohol+4 EO, and the modifiedDrave's test was performed on this solution. The result is displayed inthe Table below.

TABLE 12 Clarity interval Sinking time Formulation (° C.) pH (s) C 0-4510.5 5

The formulation containing the phosphated 2-propylheptanol+5 EO as ahydrotrope for the ethoxylate had a good wetting ability, whereas forthe different components alone, the wetting time was >420 s. TheC₉-C₁₁-alcohol is not soluble in this alkaline medium without ahydrotrope, and the phosphated 2-propylheptanol+5 EO has no good wettingability on its own. When the hydrotrope is added, the nonionicsurfactant is solubilised, and it is then able to exert its wettingability.

EXAMPLE 7

In the syntheses described below a 1,000 cm³ flange flask equipped withan anchor stirrer was used. The reactor was heated by an electricalheater equipped with a thermostat. A slight flow of nitrogen was appliedduring the reaction. The polyphosphoric acid (PPA) used wasPolyphosphoric acid 116, 84% equivalent in P₂O₅ (Albright & Wilson).

1) 2-propylheptanol+PPA

2-propylheptanol (222.47 g, 1.41 mole) was charged and heated to 45° C.PPA (254.09 g) was added from a 60 ml syringe and the exothermicreaction was kept at 55-70° C. while stirring at 240 r/min. PPA wasadded during a period of 1 hour. The reaction was then left for 2 h at60° C. and with stirring at 300 r/min. After the post-reaction water(5.0 g) was added to hydrolyse the remaining PPA, after which the acidwas neutralised with KOH (274.4 g) dissolved in 555.0 g water.

2) 2-propylheptanol+3 EO +PPA

2-propylheptanol+3 EO (295.63 g, 1.02 mole) was charged and heated to45° C. PPA (184.95 g) was added from a 60 ml syringe and the exothermicreaction was kept at 55-70° C. while stirring at 240 r/min. PPA wasadded during a period of 1 hour. The reaction was then left for 2 h at60° C. and with stirring at 300 r/min. After the post-reaction water(5.0 g) was added to hydrolyse the remaining PPA, after which the acidwas neutralised with KOH (191 g) dissolved in 454 g water.

3) 2-propylheptanol+5 EO+PPA

2-propylheptanol+5 EO (307.71 g, 0.81 mole) was charged and heated to45° C. PPA (148 g) was added from a 60 ml syringe and the exothermicreaction was kept at 55-70° C. while stirring at 240 r/min. PPA wasadded during a period of 1 hour. The reaction was then left for 2 h at60° C. and with stirring at 300 r/min. After the post reaction water(5.0 g) was added to hydrolyse the remaining PPA, after which 374.02 gacid were neutralised with KOH (132.37 g) dissolved in 517 g water.

1. A phosphated 2-propylheptanol alkoxylate wherein the alkoxylate is ahydrotrope and on average comprises 2 to 4 ethyleneoxy units, saidphosphated alkoxylate comprising two or more products of the followingformulae present in a mixture

wherein M is H, a monovalent metal ion or R₁R₂R₃R₄N⁺, where R₁, R₂, R₃,and R₄ are H, an alkyl group with 1-4 carbon atoms or —CH₂CH₂OH, and cis a number 2-4,

wherein n is 1-3 and M and c have the same meaning as above,

wherein M and c have the same meaning as above, and

wherein M and c have the same meaning as above, and wherein II ispresent in an amount of at least 60% by weight of the mixture.
 2. Thephosphated alkoxylate of claim 1 wherein II is present in an amount ofat least 80% by weight of the mixture.
 3. An industrial hard surfacecleaner comprising the phosphated alkoxylate of claim
 1. 4. Adishwashing detergent comprising the phosphated alkoxylate of claim 1.5. A vehicle cleaning composition comprising the phosphated alkoxylateof claim 1.